Thinking about my truck situation now makes my head spin with the amount of them I have had over the years. I used to trade in about every 3 to 4 years. Currently have f150. Before that f350 diesel. Had that one for about 10 years and over 200,000 miles. Had 2 other 3/4 gassers (chev 2500 and f250) mixed in too. F350 was the best truck I ever owned. 6.4 powerstroke only had a few minor emission related issues. Although it seems others with the engine had more. I pulled fishouse and 20 foot fiberglass boat. And drove to work and kids sports etc as a daily driver. Not the best daily driver, but I made it work.
Here is my take….if in your position I would look for 1 ton diesel. But, you are oviously gonna be limited on inventory. Imo all the bigger HD trucks ride rougher than say an f150. But I honestly can’t tell the difference in 3/4 ton and 1 ton. Have ridden in plenty and realistically its not that bad, especially these new ones. With the amount of driving and pulling it seems you are gonna do diesel is preferred. Im not sure the price difference between a similarly equipped f250 and f350 persay, but the cost of tabs in the long run is gonna save you some cash.
Good luck and have fun. I wish I was in your position!!!👍
Matt